Ganglioside GA2 (d18:1/18:0) (BioDeep_00000027959)

   

human metabolite Endogenous


代谢物信息卡片


N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-5-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]octadecanimidate

化学式: C56H104N2O18 (1092.7283764000001)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)O)NC(=O)C)O)O)O)O)C(C=CCCCCCCCCCCCCC)O
InChI: InChI=1S/C56H104N2O18/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-44(64)58-39(40(63)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)37-71-55-50(69)48(67)53(42(35-60)73-55)76-56-51(70)49(68)52(43(36-61)74-56)75-54-45(57-38(3)62)47(66)46(65)41(34-59)72-54/h30,32,39-43,45-56,59-61,63,65-70H,4-29,31,33-37H2,1-3H3,(H,57,62)(H,58,64)/b32-30+/t39-,40+,41+,42+,43+,45+,46-,47+,48+,49+,50?,51+,52-,53+,54-,55+,56-/m0/s1

描述信息

Ganglioside GA2 (d18:1/18:0) is a glycosphingolipid (ceramide and oligosaccharide)or oligoglycosylceramide with one or more sialic acids (i.e. n-acetylneuraminic acid) linked on the sugar chain. It is a component the cell plasma membrane which modulates cell signal transduction events. Gangliosides have been found to be highly important in immunology. Ganglioside GA2 carries a net-negative charge at pH 7.0 and is acidic. Gangliosides can amount to 6\\% of the weight of lipids from brain, but they are found at low levels in all animal tissues. Gangliosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Gangliosides are very similar to globosides except that they also contain N-acetyl neuraminic acid (NANA) in varying amounts. The specific names for the gangliosides provide information about their structure. The letter G refers to ganglioside, and the subscripts M, D, T and Q indicate that the molecule contains mono-, di-, tri and quatra-sialic acid. The numbered subscripts 1, 2 and 3 refer to the carbohydrate sequence that is attached to the ceramide. In particular, 1 stands for GalGalNAcGalGlc-ceramide, 2 stands for GalNAcGalGlc-ceramide and 3 stands for GalGlc-ceramide. Deficiencies in lysosomal enzymes that degrade the carbohydrate portions of various gangliosides are responsible for a number of lysosomal storage diseases such as Tay-Sachs disease, Sandhoff disease, and GM1 gangliosidosis. The carbohydrate portion of the ganglioside GM1 is the site of attachment of cholera toxin, the protein secreted by Vibrio cholerae.

同义名列表

12 个代谢物同义名

N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-5-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]octadecanimidate; N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-5-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]octadecanamide; GalNAc-beta1->4gal-beta1->4GLC-beta1->1cer; Bissulfogangliotetraosylceramide; Ganglioside GA2 (d18:1/18:0); ganglio-N-Triaosylceramide; Gangliotriosylceramide; g(a2) Ganglioside; GA2 ganglioside; Glycolipid g; asialo GM2; GA2



数据库引用编号

3 个数据库交叉引用编号

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代谢反应

0 个相关的代谢反应过程信息。

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1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

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文献列表

  • Eugeniy Smorodin, Boris Sergeyev, Oleg Kurtenkov, Tatiana Kuznetsova, Julia Geller. IgG Antibodies to GlcNAcβ and Asialo-GM2 (GA2) Glycans as Potential Markers of Liver Damage in Chronic Hepatitis C and the Efficacy of Antiviral Treatment. Disease markers. 2018; 2018(?):4639805. doi: 10.1155/2018/4639805. [PMID: 30627223]
  • Christian H Schweppe, Petra Hoffmann, Jerzy-Roch Nofer, Gottfried Pohlentz, Michael Mormann, Helge Karch, Alexander W Friedrich, Johannes Müthing. Neutral glycosphingolipids in human blood: a precise mass spectrometry analysis with special reference to lipoprotein-associated Shiga toxin receptors. Journal of lipid research. 2010 Aug; 51(8):2282-94. doi: 10.1194/jlr.m006759. [PMID: 20444989]
  • Yanfeng Chen, Jeremy Allegood, Ying Liu, Elaine Wang, Begoña Cachón-Gonzalez, Timothy M Cox, Alfred H Merrill, M Cameron Sullards. Imaging MALDI mass spectrometry using an oscillating capillary nebulizer matrix coating system and its application to analysis of lipids in brain from a mouse model of Tay-Sachs/Sandhoff disease. Analytical chemistry. 2008 Apr; 80(8):2780-8. doi: 10.1021/ac702350g. [PMID: 18314967]
  • J Busse, E Hartmann, C A Lingwood. Receptor affinity purification of a lipid-binding adhesin from Haemophilus influenzae. The Journal of infectious diseases. 1997 Jan; 175(1):77-83. doi: 10.1093/infdis/175.1.77. [PMID: 8985199]
  • K Tadano-Aritomi, H Kubo, P Ireland, T Kasama, S Handa, I Ishizuka. Structural characterization of a novel mono-sulfated gangliotriaosylceramide containing a 3-O-sulfated N-acetylgalactosamine from rat kidney. Glycoconjugate journal. 1996 Apr; 13(2):285-93. doi: 10.1007/bf00731503. [PMID: 8737253]
  • T Kobayashi, K Honke, S Gasa, Y Saga, T Miyazaki, K Tadano-Aritomi, I Ishizuka, A Makita. Enzymatic sulfation of gangliotriaosylceramide in human renal cancer cells. Journal of biochemistry. 1995 May; 117(5):987-92. doi: 10.1093/oxfordjournals.jbchem.a124831. [PMID: 8586644]
  • J K Hidari, S Ichikawa, K Furukawa, M Yamasaki, Y Hirabayashi. beta 1-4N-acetylgalactosaminyltransferase can synthesize both asialoglycosphingolipid GM2 and glycosphingolipid GM2 in vitro and in vivo: isolation and characterization of a beta 1-4N-acetylgalactosaminyltransferase cDNA clone from rat ascites hepatoma cell line AH7974F. The Biochemical journal. 1994 Nov; 303 ( Pt 3)(?):957-65. doi: 10.1042/bj3030957. [PMID: 7980468]
  • Y Y Wu, J M Lockyer, E Sugiyama, N V Pavlova, Y T Li, S C Li. Expression and specificity of human GM2 activator protein. The Journal of biological chemistry. 1994 Jun; 269(23):16276-83. doi: . [PMID: 8206933]
  • H B Sheth, K K Lee, W Y Wong, G Srivastava, O Hindsgaul, R S Hodges, W Paranchych, R T Irvin. The pili of Pseudomonas aeruginosa strains PAK and PAO bind specifically to the carbohydrate sequence beta GalNAc(1-4)beta Gal found in glycosphingolipids asialo-GM1 and asialo-GM2. Molecular microbiology. 1994 Feb; 11(4):715-23. doi: 10.1111/j.1365-2958.1994.tb00349.x. [PMID: 7910939]
  • H C Krivan, B Nilsson, C A Lingwood, H Ryu. Chlamydia trachomatis and Chlamydia pneumoniae bind specifically to phosphatidylethanolamine in HeLa cells and to GalNAc beta 1-4Gal beta 1-4GLC sequences-found in asialo-GM1 and asial-GM2. Biochemical and biophysical research communications. 1991 Mar; 175(3):1082-9. doi: 10.1016/0006-291x(91)91676-4. [PMID: 2025240]
  • J Ledvinova, M Iwamori, Y Nagai. Characteristic binding of human plasma apolipoprotein B to gangliotetraosylceramide and gangliotriaosylceramide. European journal of biochemistry. 1990 Dec; 194(2):507-11. doi: 10.1111/j.1432-1033.1990.tb15645.x. [PMID: 1702710]
  • N Strömberg, K A Karlsson. Characterization of the binding of Actinomyces naeslundii (ATCC 12104) and Actinomyces viscosus (ATCC 19246) to glycosphingolipids, using a solid-phase overlay approach. The Journal of biological chemistry. 1990 Jul; 265(19):11251-8. doi: NULL. [PMID: 2358461]
  • T Yamanaka, Y Hirabayashi, M Hirota, M Kaneko, M Matsumoto, N Kobayashi. Detection of gangliotriaose-series glycosphingolipids in serum of cord blood and patients with neuroblastoma by a sensitive TLC/enzyme-immunostaining method. Biochimica et biophysica acta. 1987 Jul; 920(2):181-4. doi: . [PMID: 3300782]
  • Y Ohashi, M Iwamori, T Ogawa, Y Nagai. Analysis of long-chain bases in sphingolipids by positive ion fast atom bombardment or matrix-assisted secondary ion mass spectrometry. Biochemistry. 1987 Jun; 26(13):3990-5. doi: 10.1021/bi00387a037. [PMID: 3651429]
  • Y Okada, H Matsuura, S Hakomori. Inhibition of tumor cell growth by aggregation of a tumor-associated glycolipid antigen: a close functional association between gangliotriaosylceramide and transferrin receptor in mouse lymphoma L-5178Y. Cancer research. 1985 Jun; 45(6):2793-801. doi: NULL. [PMID: 2985252]
  • D L Urdal, I Kawase, C S Henney. NK cell-target interactions: approaches towards definition of recognition structures. Cancer metastasis reviews. 1982; 1(1):65-81. doi: 10.1007/bf00049481. [PMID: 7185420]